Article
Chemistry, Organic
Xinyu Yao, Ziyi Li, Haibo Mei, Jorge Escorihuela, Vadim A. Soloshonok, Jianlin Han
Summary: A new S(N)2' reaction type between MBH ester and sulfonyl anion has been developed, in which the sulfonyl anion is generated in situ via detrifluoroacetylation. The reaction proceeds through C-C and C-S bond cleavage to generate corresponding anions, which then react with the MBH ester. The reaction features operational simplicity, wide substrate scope, high yields, and excellent stereoselectivity, providing an efficient way to obtain beta,gamma-unsaturated sulfones.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Koushik Patra, Mallu Kesava Reddy, Sumitava Mallik, Mahiuddin Baidya
Summary: The nucleophilic reactivity of alpha,alpha-difluorinated gem-diols has been utilized to selectively synthesize biologically relevant 1,4-dihydropyridines and 3,4-dihydro-2-pyridones adorned with the valuable gem-difluoromethylene motif. The method is scalable, high yielding, and compatible with a wide range of substrates and functional groups. Additionally, the synthesis of difluorinated oxa-azabicyclo [3.3.1] nonane frameworks has been demonstrated through product diversification.
Article
Chemistry, Organic
Hai-Xiang Zeng, Xiao-Wen Zhang, Qi-Yang Li, Wen-Bo Liu
Summary: An enantioselective Ni-catalyzed syn-hydrocyclization reaction was developed for the synthesis of α-hydroxy γ-lactams. By using Ni(OTs)(2)·6H(2)O/(S,S)-Me-Duphos as a precatalyst and (EtO)2MeSiH as a hydride source, a wide range of enantioenriched γ-lactams with fully substituted stereogenic centers were obtained in 32-84% yields with 87.5:12.5-97:3 er. This research provides a regioselective functionalization of alkynes and offers an efficient strategy for accessing functional group-enriched chiral heterocycles.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Wen-Yan Xu, Yu-Jie Li, Tian-Jun Gong, Yao Fu
Summary: In this study, a Cu/Pd-catalyzed borodifluorovinylation reaction was used to synthesize conjugated gem-difluoroalkene scaffolds with good functional group compatibility, using alkynes, difluoroethylene bromide, and B2pin2 as chemical feedstock.
Article
Chemistry, Multidisciplinary
Yaxin Zeng, Hui Yang, Jiayi Du, Qin Huang, Guoliang Huang, Ying Xia
Summary: The control of linear/branched selectivity in transition-metal catalyzed allyl-allyl cross-coupling reactions has been investigated in this study. It has been found that the terminal/internal regioselectivity can be switched by fine-tuning the rhodium catalytic system. Different types of 1,5-dienes are produced with good yields, exhibiting isomerized terminal, internal, and terminal regioselectivity.
Article
Chemistry, Multidisciplinary
Zhiyuan Fu, Jianping Zhu, Songjin Guo, Aijun Lin
Summary: The palladium-catalyzed allylic alkylation dearomatization reaction provides an efficient route to access compounds with naphthalene and indole moieties, featuring high yields and Z-selectivity. This reaction benefits from a wide substrate scope and good functional group tolerance, allowing for the synthesis of complex molecules with quaternary carbon centers.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Yanhui Wang, Qiao Ma, Gavin Chit Tsui
Summary: A highly diastereoselective Pd(0)-catalyzed synthesis of difluorinated 1,3-dienes has been described, utilizing a stereoselective twofold Pd-catalyzed Miyaura borylation/Suzuki-Miyaura cross-coupling of the C-F bond. The modular synthesis of symmetrical and unsymmetrical difluorinated 1,3-dienes is achievable through different reaction pathways.
Article
Chemistry, Organic
Yanling Zheng, Yang Long, Huihua Gong, Jiaqi Xu, Chunchun Zhang, Haiyan Fu, Xueli Zheng, Hua Chen, Ruixiang Li
Summary: In this study, the divergent transformations of 1,3-diols with arylhydrazines were reported, which selectively synthesized pyrazoles and 2-pyrazolines via acceptorless dehydrogenative coupling reactions using Ru3(CO)12/NHC-phosphinephosphine catalytic systems. The reactions showed low catalyst loading, high selectivity, wide substrate scope, and good yields, with only water and hydrogen gas (H2) as the byproducts.
Article
Chemistry, Organic
Jie Jia, Fushan Yuan, Zihao Zhang, Xuejiao Song, Fangdong Hu, Ying Xia
Summary: In this study, a copper-catalyzed reaction of gem-fluorinated cyclobutenes with bis(pinacolato)diboron was reported, leading to the formation of B,F-bifunctional 1,3-dienes. The transformation was achieved through a sequence of reactions, allowing for the stereoselective synthesis of highly functionalized 1,3-dienes.
Article
Chemistry, Physical
Martin Soto, Vicente Gotor-Fernandez, Humberto Rodriguez-Solla, Walter Baratta
Summary: The transfer hydrogenation of flavanones and ortho-hydroxychalcones catalyzed by ruthenium pincer complexes allows the synthesis of ortho-hydroxy 1,3-diarypropanols with high yield and selectivity. The amount of co-catalyst is crucial for the reduction reaction, while using pincer catalysts with specific ligands can achieve high enantiomeric excess and moderate conversion rates in the reduction of flavanones.
Article
Chemistry, Physical
Yingqi Xia, Yingtang Ning, Minjie Liu, Fen -Er Chen
Summary: A poly(ethylene glycol) supported amino alcohol has been developed as a chiral ligand for the copper-catalyzed asymmetric nitrolaldol reaction. The catalyst enables the synthesis of syn-2-nitro-1,3-diols with high yields and stereoselectivities. The PEG moiety allows for easy purification and recycling of the catalyst.
JOURNAL OF CATALYSIS
(2023)
Review
Chemistry, Multidisciplinary
Keisuke Nogi, Hideki Yorimitsu
Summary: The retroallylation and deallylation of allylic compounds are intriguing methods for cleavage of C-C sigma bonds, generating valuable allylic metal compounds and serving as protective groups for acidic C-H bonds. These transformations offer wide application in regio-, stereo-, and enantioselective synthesis.
Article
Chemistry, Organic
Lukas Durina, Tomas Malatinsky, Jan Moncol, Ondrej Zaborsky, Robert Fischer
Summary: In this study, the reaction of 3,4-trans-isoxazolidine4,5-diols with Grignard reagents is investigated for the first time, leading to the synthesis of anti,syn-gamma-(hydroxyamino)-alpha,beta-diols with good diastereoselectivities. These (hydroxyamino)diols can serve as valuable precursors for the synthesis of biologically active compounds.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Inorganic & Nuclear
Christian A. M. R. van Slagmaat, Teresa Faber, Khi Chhay Chou, Alfonso J. Schwalb Freire, Darya Hadavi, Peiliang Han, Peter J. L. M. Quaedflieg, Gerard K. M. Verzijl, Paul L. Alsters, Stefaan M. A. De Wildeman
Summary: This study presents the hydrogenative conversion of biobased platform molecules to their corresponding diols using a pre-activated Knolker-type iron catalyst. The catalyst demonstrates high selectivity for ketone reduction without inducing dehydration, and the cis-trans ratio of products can be substantially affected by different ligand substituents. Additionally, the catalytic system shows decent compatibility with various structurally related substrates.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Organic
Fan Wu, Shengjun Liu, Xiaoqing Lv, Mei Pan, Xiaoqin Liu, Jinpeng Zhang, Liangce Rong
Summary: A simple and efficient method for synthesis of 1,4-diketones has been developed using novel and efficient electrochemical radical reactions. The reactions were carried out under catalyst-free and oxidant-free conditions, and resulted in a wide range of substrates and good group tolerance. The obtained 1,4-diketones can be easily transformed into pyrrole and furan derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
